6-(4-氯苯基)-2-氧代-1,2-二氢吡啶-3-羧酸 | 147269-16-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 中文名称: 6-(4-氯苯基)-2-氧代-1,2-二氢吡啶-3-羧酸
• 英文名称: 6-(4-Chloro-phenyl)-2-oxo-1,2-dihydro-pyridine-3-carboxylic acid
• 英文别名: 6-(4-Chlorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid；6-(4-chlorophenyl)-2-oxo-1H-pyridine-3-carboxylic acid
• CAS: 147269-16-7
• 化学式: C₁₂H₈ClNO₃
• mdl: MFCD06653399
• 分子量: 249.653
• InChiKey: CBGGWZGPODAQIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(4-氯苯基)-2-氧代-1,2-二氢吡啶-3-羧酸 在 二苯基磷酸 、 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 生成 [6-(4-Chloro-phenyl)-2-oxo-1,2-dihydro-pyridin-3-yl]-carbamic acid benzyl ester
  参考文献：
  名称：

  Nonpeptidic Inhibitors of Human Leukocyte Elastase. 2. Design, Synthesis, and in vitro Activity of a Series of 3-Amino-6-aryl-2-oxopyridyl Trifluoromethyl Ketones

  摘要：

  A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

  DOI：

  10.1021/jm00046a015
• 作为产物：
  描述：

  6-(4-氯苯基)-2-氧代-1,2-二氢吡啶-3-腈 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 生成 6-(4-氯苯基)-2-氧代-1,2-二氢吡啶-3-羧酸
  参考文献：
  名称：

  Nonpeptidic Inhibitors of Human Leukocyte Elastase. 2. Design, Synthesis, and in vitro Activity of a Series of 3-Amino-6-aryl-2-oxopyridyl Trifluoromethyl Ketones

  摘要：

  A series of potent nonpeptidic inhibitors of the enzyme human leukocyte elastase (HLE) is reported. These inhibitors contain a 3-amino-2-pyridone ring as a central template in which the pyridone carbonyl and 3-position NH group are thought to form important hydrogen bonding interactions with the Val-216 residue of HLE. Substitution of the 6-position of the pyridone ring by various alkyl and aryl groups was found to afford increases in the in vitro potency of these inhibitors. A 6-position phenyl group, compound 10f, was found to result in a large increase in binding affinity, which was not obtained when the phenyl group was placed in either the 4- or 5-position of the molecule. Compound 10f was found to have good selectivity for HLE over other proteolytic enzymes, with the exception of bovine pancreatic chymotrypsin (BPC). Substitution of the 6-phenyl group in these molecules was found to decrease binding affinity for BPC without adversely affecting affinity for HLE.

  DOI：

  10.1021/jm00046a015

文献信息

• [DE] VERWENDUNG AUSGEWÄHLTER PYRIDONCARBOXAMIDE ODER DEREN SALZEN ALS WIRKSTOFFE GEGEN ABIOTISCHEN PFLANZENSTRESS<br/>[EN] USE OF SELECTED PYRIDONE CARBOXAMIDES OR SALTS THEREOF AS ACTIVE SUBSTANCES AGAINST ABIOTIC PLANT STRESS<br/>[FR] UTILISATION DE PYRIDONE-CARBOXAMIDES SÉLECTIONNÉS OU DE LEURS SELS COMME PRINCIPES ACTIFS CONTRE LE STRESS ABIOTIQUE DES PLANTES
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2016096942A1

  公开（公告）日：2016-06-23

  Verwendung substituierter Pyridoncarboxamide der allgemeinen Formel (I) oder deren Salze, wobei die Reste in der allgemeinen Formel (I) den in der Beschreibung gegebenen Definitionen entsprechen, zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags.